WO1993013112A1 - Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides - Google Patents
Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides Download PDFInfo
- Publication number
- WO1993013112A1 WO1993013112A1 PCT/EP1992/002894 EP9202894W WO9313112A1 WO 1993013112 A1 WO1993013112 A1 WO 1993013112A1 EP 9202894 W EP9202894 W EP 9202894W WO 9313112 A1 WO9313112 A1 WO 9313112A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- bleaching
- alkenyl
- alcohol
- stabilizers
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 26
- 238000004061 bleaching Methods 0.000 title claims abstract description 23
- -1 alkenyl glycosides Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 18
- 229930182470 glycoside Natural products 0.000 title claims abstract description 8
- 239000003381 stabilizer Substances 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims abstract description 7
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 7
- 239000008139 complexing agent Substances 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 11
- 235000000346 sugar Nutrition 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000004411 aluminium Substances 0.000 abstract 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 15
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 229960001031 glucose Drugs 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001323 aldoses Chemical class 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 229930182478 glucoside Natural products 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- IKYKEVDKGZYRMQ-PDBXOOCHSA-N (9Z,12Z,15Z)-octadecatrien-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCO IKYKEVDKGZYRMQ-PDBXOOCHSA-N 0.000 description 1
- TVPWKOCQOFBNML-SEYXRHQNSA-N (z)-octadec-6-en-1-ol Chemical compound CCCCCCCCCCC\C=C/CCCCCO TVPWKOCQOFBNML-SEYXRHQNSA-N 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- HLCFGWHYROZGBI-JJKGCWMISA-M Potassium gluconate Chemical compound [K+].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O HLCFGWHYROZGBI-JJKGCWMISA-M 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ALSTYHKOOCGGFT-MDZDMXLPSA-N oleyl alcohol Chemical compound CCCCCCCC\C=C\CCCCCCCCO ALSTYHKOOCGGFT-MDZDMXLPSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004224 potassium gluconate Substances 0.000 description 1
- 229960003189 potassium gluconate Drugs 0.000 description 1
- 235000013926 potassium gluconate Nutrition 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019351 sodium silicates Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
Definitions
- the invention relates to a process for bleaching alkyl and / or alkenyl oligoglycosides, in which the bleaching is carried out with peroxygen compounds in the presence of aluminum ions, alkali silicates, sugar acids and / or organic complexing agents as stabilizers.
- European Patent EP 0 165 721 B1 suggests treating alkyl glycosides first with hydrogen peroxide or other peroxygen compounds and then with an SO 2 source.
- a process for bleaching alkyl glucosides is known from European patent application EP 0 338 151 A1, in which the products are subjected to a hydrogenation, for example with sodium boranate.
- the object of the invention was therefore to develop an improved process for bleaching alkyl and / or alkenyl oligoglyosides which is free from the disadvantages described.
- the invention relates to a process for bleaching alkyl and / or alkenyl glycosides with the aid of peroxygen compounds, which is characterized in that the bleach is selected in the presence of stabilizers from the group consisting of aluminum ions, alkali metal silicates, sugar acids and organic complexing agents is formed.
- stabilizers from the group consisting of aluminum ions, alkali metal silicates, sugar acids and organic complexing agents.
- R! for an aliphatic, linear or branched alkyl and / or alkenyl radical with 6 to 22 carbon atoms
- the glycose unit [G] can be derived from aldoses or ketoses. Because of the better reactivity, the reducing saccharides, the aldoses, are preferably used. Among the aldoses, glucose is particularly suitable because of their easy access and technical availability.
- the preferred bleached alkyl and / or alkenyl oligoglycosides are therefore the alkyl and / or alkenyl oligoglucosides.
- the alkyl radical R 1 can be derived from primary alcohols having 6 to 22, preferably 12 to 18, carbon atoms. Typical examples are capronic alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palm oleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, arachyl alcohol, technical alcohols, gadoleyl alcohol, and mixtures thereof, gadoleyl alcohol of natural fats and oils, for example palm oil, palm kernel oil, coconut oil or beef tallow.
- capronic alcohol caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palm oleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol,
- alkyl oligoglycosides of the formula (I) in which R 1 is an alkyl radical having 12 to 18 carbon atoms. ato en, [G] stands for a glucose residue and / or p for numbers from 1.1 to 3.0.
- the bleaching is carried out in the presence of peroxygen compounds.
- peroxygen compounds Typical examples of this are perborates, percarbonates and in particular hydrogen peroxide, which can be used in the form of an aqueous 5 to 70, preferably 15 to 35% by weight solution.
- concentration of the peroxygen compounds can be 1 to 5, preferably 2 to 3% by weight, based on the solids content of the alkyl or alkenyl oligoglycoside paste to be bleached.
- Aluminum ions, alkali silicates, sugar acids and / or organic complexing agents come into consideration as stabilizers.
- the aluminum ions can be added to the peroxygen compounds in the form of salts, for example sulfates, carbonates, silicates or phosphates.
- alkali silicates are sodium and / or potassium silicates (“water glass”), in which an average of 2 to 4 moles of silicon dioxide per mole of alkali oxide.
- sugar acids gluconic acid, glucaric acid, glucoronic acid and glucoheptonic acid and their alkali and alkaline earth salts are particularly suitable.
- organic complexing agents are phosphonic acids, such as, for example, diethylenetriaminepentamethylphosphonic acid.
- the stabilizers can be used individually or in combination in concentrations of 0.1 to 5.0, preferably 0.5 to 3.0 and in particular 1.0 to 2.0% by weight, based on the solids content of the alkyl to be bleached. or alkenyl oligoglycoside paste - are used.
- the surface-active compounds are mixed with the peroxygen compounds and the stabilizers. This can take place at ambient temperature or else at the bleaching temperature, the latter being 80 to 120, preferably 90 to 100 ° C.
- the alkyl or alkenyl oligoglycosides obtainable by the process according to the invention are light-colored and are suitable for the production of detergents, dishwashing detergents and cleaning agents and for products for hair and body care, in which they are present in amounts of 0.1 to 50, preferably 1 to 10 wt .-% - based on the agent - may be included.
- the water of reaction was continuously distilled off and the reaction was stopped after the water separation had ended and the residual content of unreacted glucose in the mixture was less than 1% by weight, based on the starting amount.
- the reaction mixture was then neutralized with magnesium oxide, the excess coconut fatty alcohol was separated off under reduced pressure (approx. 1 mbar) and at a temperature of 180 ° C. using a thin-film evaporator and the residue was pasted with water.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Detergent Compositions (AREA)
- Saccharide Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Des alkylglucosides et/ou des alcénylglucosides de teinte claire sont fabriqués au moyen de composés peroxygénés, par blanchiment en présence d'agents stabilisants choisis dans le groupe formé par les ions aluminium, les silicates alcalins, les acides sacchariques et des agents complexants organiques.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4142592.8 | 1991-12-21 | ||
| DE19914142592 DE4142592A1 (de) | 1991-12-21 | 1991-12-21 | Verfahren zur bleiche oberflaechenaktiver verbindungen |
| DEP4200850.6 | 1992-01-15 | ||
| DE19924200850 DE4200850A1 (de) | 1992-01-15 | 1992-01-15 | Verfahren zur bleiche von alkyl- und/oder alkenyloligoglycosiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993013112A1 true WO1993013112A1 (fr) | 1993-07-08 |
Family
ID=25910447
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1992/002894 WO1993013112A1 (fr) | 1991-12-21 | 1992-12-14 | Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides |
| PCT/EP1992/002895 WO1993013113A1 (fr) | 1991-12-21 | 1992-12-14 | Procede de blanchiment pour composes tensioactifs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1992/002895 WO1993013113A1 (fr) | 1991-12-21 | 1992-12-14 | Procede de blanchiment pour composes tensioactifs |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0618922A1 (fr) |
| JP (1) | JPH07502682A (fr) |
| WO (2) | WO1993013112A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996001269A1 (fr) * | 1994-07-06 | 1996-01-18 | Henkel Kommanditgesellschaft Auf Aktien | Procede de production d'agents tensioactifs de couleur claire |
| EP0775226B2 (fr) † | 1994-08-10 | 2001-04-18 | Woellner-Silikat Gmbh | Utilisation d'un concentre d'agents stabilisants pour solutions aqueuses de blanchiment et de traitement a base de peroxyde d'hydrogene et/ou d'autres composes peroxo organiques et/ou inorganiques |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4432621A1 (de) | 1994-09-14 | 1996-03-21 | Huels Chemische Werke Ag | Verfahren zur Bleichung von Tensidlösungen |
| DE4432623A1 (de) | 1994-09-14 | 1996-03-21 | Huels Chemische Werke Ag | Verfahren zur Bleichung von wäßrigen Tensidlösungen |
| US5914433A (en) * | 1997-07-22 | 1999-06-22 | Uop Lll | Process for producing polymer grade olefins |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0165721A1 (fr) * | 1984-05-24 | 1985-12-27 | A.E. Staley Manufacturing Company | Régulation de couleur de glycosides |
| EP0301298A1 (fr) * | 1987-07-18 | 1989-02-01 | Henkel Kommanditgesellschaft auf Aktien | Procédé de préparation de glucosides d'alkyle |
| EP0306652A1 (fr) * | 1987-09-05 | 1989-03-15 | Hüls Aktiengesellschaft | Procédé pour la préparation de glucosides d'alkyle |
| EP0306650A1 (fr) * | 1987-09-05 | 1989-03-15 | Hüls Aktiengesellschaft | Procédé pour la préparation d'alkylglycosides |
| EP0306651A1 (fr) * | 1987-09-05 | 1989-03-15 | Hüls Aktiengesellschaft | Procédé pour la préparation d'oligoglucosides d'alkyl |
| EP0362671A1 (fr) * | 1988-10-05 | 1990-04-11 | Henkel Kommanditgesellschaft auf Aktien | Procédé direct pour la préparation des alkylglycosides |
| EP0389753A2 (fr) * | 1989-03-30 | 1990-10-03 | Hüls Aktiengesellschaft | Procédé de préparation d'alkylpolyglycosides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159657A (en) * | 1961-05-19 | 1964-12-01 | Henkel & Cie Gmbh | Preparation of light-colored sulfonated fatty acids and fatty acid derivatives |
| US3354187A (en) * | 1962-03-09 | 1967-11-21 | Henkel & Cie Gmbh | Bleaching dark-colored sulfonation products |
| DE1234709B (de) * | 1964-01-15 | 1967-02-23 | Henkel & Cie Gmbh | Kontinuierliches Verfahren zum Bleichen saurer Sulfonierungsprodukte |
| DE3319591A1 (de) * | 1983-05-30 | 1984-12-06 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur gewinnung farbstabiler hellfarbiger waessriger salzpasten von waschaktiven (alpha)-sulfofettsaeureestern |
-
1992
- 1992-12-14 WO PCT/EP1992/002894 patent/WO1993013112A1/fr active Application Filing
- 1992-12-14 EP EP93900047A patent/EP0618922A1/fr not_active Ceased
- 1992-12-14 WO PCT/EP1992/002895 patent/WO1993013113A1/fr not_active Application Discontinuation
- 1992-12-14 JP JP5511394A patent/JPH07502682A/ja active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0165721A1 (fr) * | 1984-05-24 | 1985-12-27 | A.E. Staley Manufacturing Company | Régulation de couleur de glycosides |
| EP0301298A1 (fr) * | 1987-07-18 | 1989-02-01 | Henkel Kommanditgesellschaft auf Aktien | Procédé de préparation de glucosides d'alkyle |
| EP0306652A1 (fr) * | 1987-09-05 | 1989-03-15 | Hüls Aktiengesellschaft | Procédé pour la préparation de glucosides d'alkyle |
| EP0306650A1 (fr) * | 1987-09-05 | 1989-03-15 | Hüls Aktiengesellschaft | Procédé pour la préparation d'alkylglycosides |
| EP0306651A1 (fr) * | 1987-09-05 | 1989-03-15 | Hüls Aktiengesellschaft | Procédé pour la préparation d'oligoglucosides d'alkyl |
| EP0362671A1 (fr) * | 1988-10-05 | 1990-04-11 | Henkel Kommanditgesellschaft auf Aktien | Procédé direct pour la préparation des alkylglycosides |
| EP0389753A2 (fr) * | 1989-03-30 | 1990-10-03 | Hüls Aktiengesellschaft | Procédé de préparation d'alkylpolyglycosides |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996001269A1 (fr) * | 1994-07-06 | 1996-01-18 | Henkel Kommanditgesellschaft Auf Aktien | Procede de production d'agents tensioactifs de couleur claire |
| US5858961A (en) * | 1994-07-06 | 1999-01-12 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of light-colored surfactants |
| EP0775226B2 (fr) † | 1994-08-10 | 2001-04-18 | Woellner-Silikat Gmbh | Utilisation d'un concentre d'agents stabilisants pour solutions aqueuses de blanchiment et de traitement a base de peroxyde d'hydrogene et/ou d'autres composes peroxo organiques et/ou inorganiques |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0618922A1 (fr) | 1994-10-12 |
| JPH07502682A (ja) | 1995-03-23 |
| WO1993013113A1 (fr) | 1993-07-08 |
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